Synthesis and in vitro biological activity of retinyl retinoate, a novel hybrid retinoid derivative

Bioorg Med Chem. 2008 Jun 15;16(12):6387-93. doi: 10.1016/j.bmc.2008.05.005. Epub 2008 May 6.

Abstract

A new hybrid, retinyl retinoate 1, was synthesized with a condensing reaction between retinol and retinoic acid to improve the photo-stability, and the in vitro biological activity of the hybrid was analyzed. This retinol derivative had enhanced thermal stability and decreased photosensitivity, and exhibited decreased cell toxicity compared to that of retinol. In addition, RAR activity analysis showed that retinyl retinoate 1 had higher inhibitory activity against c-Jun than retinol and showed superior effects on collagen synthesis compared to retinol. Thus, retinyl retinoate 1 may have the potential to be conveniently used as an additive in cosmetics for prevention and improvement of skin aging and medicines for the treatment of skin troubles due to its excellent stability under severe and accelerated conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cells, Cultured
  • Collagen / biosynthesis
  • Collagen / drug effects
  • Humans
  • Light
  • RNA, Messenger / metabolism
  • Receptors, Retinoic Acid / agonists
  • Receptors, Retinoic Acid / genetics
  • Receptors, Retinoic Acid / metabolism
  • Retinoids / chemical synthesis
  • Retinoids / chemistry*
  • Retinoids / pharmacology*
  • Retinyl Esters
  • Skin Aging / drug effects*
  • Transcription Factor AP-1 / antagonists & inhibitors
  • Tretinoin / chemistry*
  • Tretinoin / pharmacology
  • Vitamin A / chemistry*
  • Vitamin A / pharmacology

Substances

  • RNA, Messenger
  • Receptors, Retinoic Acid
  • Retinoids
  • Retinyl Esters
  • Transcription Factor AP-1
  • retinoic acid binding protein II, cellular
  • Vitamin A
  • Tretinoin
  • retinyl retinoate
  • Collagen